Baeyer–Villiger oxidation under Payne epoxidation conditions

Bradley, Tyne D. and Dragan, Andrei and Tomkinson, Nicholas C.O. (2015) Baeyer–Villiger oxidation under Payne epoxidation conditions. Tetrahedron, 71 (42). 8155–8161. ISSN 0040-4020 (

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A novel method for the Baeyer–Villiger oxidation of ketones has been developed and optimized. The transformation involves a transition metal-free activation of hydrogen peroxide under Payne epoxidation conditions. Reaction of a ketone with hydrogen peroxide in the presence of a nitrile under mildly basic reaction conditions leads to the corresponding ester. The transformation has been successfully applied to a range of ketones in moderate to excellent yields (30–91 and good to excellent regioselectivities (7:1 to 20:1).